Phosgene → 4-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carbonyl chloride

HRID 271868

Reaction equation

HRID 271868 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[Cl-].[Cl-].[O:7]=[C:8]1[NH:16][C:11]2=[NH+:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]1[CH:17]1[CH2:22][CH2:21][NH2+:20][CH2:19][CH2:18]1.N1C(C)=CC=CC=1C.C(=O)(O)[O-].[Na+]>ClCCl>[O:7]=[C:8]1[NH:16][C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]1[CH:17]1[CH2:22][CH2:21][N:20]([C:1]([Cl:4])=[O:2])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 79372,6-LutidineHCID 516892Sodium BicarbonateHCID 178518668HCID 178518668, compound

Product 1

HCID 222932214-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carbonyl chlorideYield 49.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosgene (20% wt. in toluene; 1.8 mL, 3.43 mmol) was added to a suspension of 2-oxo-1-piperidinium-4-yl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-4-ium dichloride (100 mg, 0.343 mmol) and 2,6-lutidine (0.50 mL, 4.293 mmol) in dichloromethane (5 mL) at 0° C. After 2 h, the solution was added to saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with water (2×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Dichloromethane (10 mL) was added, and the mixture was filtered to give the title compound as a solid (48 mg). MS 281 (M+1). 1H NMR (500 MHz, (CD3)2SO) δ 11.58 (s, 1H), 7.90 (d, J=5.1 Hz, 1H), 7.67 (d, J=7.6 Hz, 1H), 7.01-6.99 (m, 1H), 4.52-4.46 (m, 1H), 4.31-4.23 (m, 2H), 3.38-3.33 (m, 1H), 3.19-3.14 (m, 1H), 2.32-2.24 (m, 2H), 1.84-1.81 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water (2×), saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionDichloromethane (10 mL) was added
  7. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-c407cfd1533c4f1f9dd232cae91af92b
Source dataset
uspto-grants-2008_11
Patent number
US07452903B2

Linked notes

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